What’s In It For You? How to Reward Yourself For Meeting Your Goals

Show yourself some love!

How can I motivate and reward myself when I am both the boss and the employee?

So, one of the skills I teach in my Plan to Thrive productivity program is how to use a four-month rolling plan to keep up your momentum. And one essential part of the rolling plan is a way to reward success.

One of the most difficult parts for some people is designing a reward that is truly motivating and appropriate. It is an exercise in knowing oneself better. Crazy, right? You’d think we’d always know what we like, what we want, what moves us. But we often don’t.

I cannot tell you how many times I’ve worked with people who say, being able to pay my bills will be my reward! (Would that launch you out of bed? Me, neither. Covers, meet head.)

Or there’s what I call “the Mercedes Syndrome,” which causes otherwise creative people to resort to some luxury trinket that really won’t motivate them at all. Sometimes those trinkets even bring more problems than rewards. (Can you say “repair costs?”)

And here’s my own recent story: In January I made a four-month rolling plan that included doing something¬† important. Not fun, not richly rewarding, but difficult, necessary, and important. I thought about what I would give myself when I achieved this milestone. And things began to get a little bit interesting.

Some typical rewards — a massage, a new adventure such as my recent sky-dive, a red briefcase, gold glasses, a weekend away — seemed all wrong for this assignment. I needed something that would respect the difficult aspects of my assignment and not cheapen my effort with trivial rewards.

I sat with the question for as long as it took (often the key to success.) And finally it hit me: I envisioned a group of professional women whom I admire joining me for a social occasion, like afternoon tea, and celebrating the completion of my gnarly goal.

Yes, that was it. To receive their support and the looks that I anticipated around that tea table, I was willing to keep moving until the thing was done.

I didn’t finish in the winter or spring, but by the end of summer, it was complete.

And then I hit a wall. I found it more difficult to invite my friends to tea than I had found jumping out of an airplane at 15,000 feet. Entrepreneurship is nothing if not an education in self-knowledge.

I enlisted the help of a friend, who coaxed me through the process of setting a date and making the invitation for my reward. And it was perfect.

Last Friday I sat at a corner table in Lovejoy’s Tea Room in San Francisco surrounded by some of the most interesting women you could ever meet:

Marnie Reasor, homeopathic practitioner (check back soon to see her new website!)

Helen Ingwersen, professional organizer for San Mateo, Santa Clara, and other parts of the San Francisco Peninsula

Katherine Krebs, meeting planner extraordinaire

Olivia Kuser, artist/gardener/savvy auntie, and all-around wise and beautiful voice

Deborah Frangquist, vocations coach

Yuriko Romer, documentary filmmaker whose project about the most famous woman in judo was recently funded on Kickstarter

Kathy Wadill, author of one of my very favorite organizing books

As I looked around the table, I thought of the women who were not able to join us, and the inspiration of their work was part of my reward, too.

I considered taking a photo of the group around the table to share with my readers, but decided against it. The experience was the reward; no photos necessary. But trust me, it was a beautiful sight!

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